• Bulletin of the Korean Chemical Society
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• v.24 no.8
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• pp.1232-1234
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• 2003

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.399.1-399.1
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• 2002

The chiral stationary phase derived from (＋) (18-crown-6)-2.3, 11.12-tetracarboxylic acid (18-C-6- TA) as a chiral selector has been employed for resolution of several $\alpha$-amino acids in HPLC. In a quest for the origin of chiral recognition of $\alpha$-amino acids in the presence of 18-C-6- T, A, as a chiral selector, these interactions responsible for the differential affinities shown toward enantioners were investigated by NNR spectroscopy. (omitted)

• Journal of Integrative Natural Science
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• v.9 no.1
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• pp.28-34
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• 2016

A number of chiral selectors have been developed and applied for enantiomer separation of a variety of chiral compounds. Among these chiral selectors are chiral crown ethers, a class of synthetic host polyether molecules that bind protonated chiral primary amines with high selectivity and affinity. In this paper, two important chiral crown ethers as chiral selectors of bis-(1,1'-binaphthyl)-22-crown-6 and (18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) are focused. They have been widely used to resolve the enantiomers of chiral compounds containing a primary amino moiety using chiral stationary phases (CSPs) or chiral selectors by high-performance liquid chromatography (HPLC), capillary electrophoresis (CE) and so on in chirotechnology. Also, it was described that the commercially available covalent type HPLC CSPs derived from (+)- and (-)-18-C-6-TA have been developed and successfully applied for the resolution of various primary amino compounds including amino acids.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.278.1-278.1
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• 2003

Recently, particular attention has been paid to the chiral separation of amino acid enantiomers because of their different biological activities. Hence, the high optical purity of aromatic amino acids is critical because of their important functions in the central nervous system. For the accurate chiral discrimination. we attempted to exploit the crosschecking each enantiomeric migraion orders of aromatic amino acids measured using (+)-18C6H4TA and (-)-18C6H4TA as the chiral selectors under pH 2.0, tris/citric acid buffer.

• KSBB Journal
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• v.27 no.4
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• pp.199-206
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• 2012

Chiral crown ethers are synthetic macrocyclic polyethers that bind protonated chiral primary amines with high selectivity and affinity. They have been widely used to separate or distinguish the enantiomers of chiral compounds containing a primary amino moiety by high-performance liquid chromatography, capillary electrophoresis, and NMR spectroscopy. In this paper, two important chiral crown ethers including chiral binaphthyl unit and (18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selectors are focused. And several chiral resolution techniques and their applications in chirotechnology using these chiral crown ethers with related chiral recognition mechanism studies are reviewed. Especially, it was shown that the commercially available HPLC columns based on (18-crown-6)-2,3,11,12-tetracarboxylic acid have been developed and successfully applied for the resolution of various primary amino compounds including amino acids.

• KSBB Journal
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• v.27 no.4
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• pp.232-236
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• 2012

Comparative liquid chromatographic enantiomer separation of ${\alpha}$-amino acids, their esters and primary amino compounds was performed using two chiral stationary phases (CSPs) prepared by covalently bonding (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) of the same chiral selector. In general, the separation factors and resolution factors for these analytes on CSP 1 were greater than on CSP 2, while these capacity factors on CSP 2 were quite greater than on CSP 1. Except for leucine methyl ester and phenylalanine methyl ester, the elution orders of all analytes including ${\alpha}$-amino ${\alpha}$-alkyl acids and phenylglycine alkyl esters on CSP 1 are identical to those on CSP 2. This study showed that different connecting structures for these two CSPs might influence their ability to resolve the analytes depending on their structures related to the chiral recognition mechanism.

• Bulletin of the Korean Chemical Society
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• v.33 no.10
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• pp.3481-3484
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• 2012